The goal of this research is to develop a useful synthetic methodology for catalytically producing core polycyclic ring structures using palladacycles generated from enolates. These core structures are found in biologically active molecules ranging from terpenes to alkaloids thus making them of great interest to chemists attempting the synthesis of natural products. The generality of this proposed methodology in the application of enolates to palladium cascade reactions would permit facile incorporation into synthetic strategies. The first part of the research will involve the catalytic production of bicyclic systems via intermolecular coupling of o- bromoacetophenone derviatives with alkenes and alkynes. Asymmetric reactions will also be examined. Further extension of this chemistry to aliphatic enolates will be pursued. Second, the focus will shift to intramolecular cascade reactions involving insertions of alkenes, alkynes, and nitriles into the palladacycle. Finally, a short exploration of the nature of the actual palladacycle proposed to form in this catalytic chemistry will be undertaken. The palladacycle will be isolated and studied by various spectroscopic techniques to determine its bonding and structure. The results of this research will lend insight into palladium-enolate chemistry and allow chemists a greater range of creativity in synthetic design.